Metathesis of ethyl oleate, catalyzed by WCl
6 and SnMe
4, provided diethyl 9-octadecenedioate (the desired starting material for the synthesis of civetone) in 99% yield. Dieckmann
condensation of diethyl 9-octadecenedioate gave 2-ethoxycarbonyl-9-cycloheptadecenone (63% yield), the hydrolysis-decarboxylation
reaction of which yielded civetone (93%). Identification of all products was by
1H nuclear magnetic resonance, infrared and mass spectroscopic data. This is the first report of the synthesis of civetone
from palm oil-derived products.
Key Words Civet - civetone - diethyl 9-octadecenedioate - 2-ethoxycarbonyl-9-cycloheptadecenone - ethyl oleate - metathesis - palm oil